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First 90 Days as a CTO

First 30 Days: Learn & Assess

1. Understand Business Goals & Strategy

  • Meet with the CEO, leadership team, and key stakeholders.
  • Learn about the company’s mission, vision, and financials.
  • Understand how technology supports business objectives.

2. Assess the Technology Landscape

  • Review existing architecture, infrastructure, tech stack, and scalability.
  • Identify technical debt, bottlenecks, and security risks.
  • Evaluate ongoing projects and upcoming releases.

3. Engage with the Engineering Team

  • Build relationships with key engineers and managers.
  • Understand team structure, culture, strengths, and weaknesses.
  • Assess engineering practices, development workflows, and technical debt.

4. Understand Product & Customer Needs

  • Engage with product managers and understand the roadmap.
  • Learn about customer pain points and gather feedback.
  • Identify gaps in the product and technology strategy.

Days 31-60: Plan & Strategise

5. Define Your Technology Vision

  • Align your vision with business objectives and growth plans.
  • Define key technology priorities (e.g. scalability, security, AI adoption).
  • Outline a high-level strategy for improvements and innovation.

6. Evaluate the Team & Processes

  • Identify skill gaps and potential hiring needs.
  • Assess whether Agile, DevOps, and CI/CD practices are optimised.
  • Recommend improvements for engineering productivity and collaboration.

7. Ensure Security & Compliance

  • Conduct a security audit to identify vulnerabilities.
  • Ensure compliance with industry standards (GDPR, ISO 27001, SOC 2).
  • Establish or refine cybersecurity policies.

8. Stakeholder Communication & Quick Wins

  • Present findings and recommendations to the leadership team.
  • Identify and execute quick wins to build credibility.
  • Foster alignment between product, engineering, and business teams.

Days 61-90: Execute & Deliver

9. Build the Roadmap & Start Execution

  • Develop a technology roadmap with clear priorities.
  • Start tackling key technical debt and process inefficiencies.
  • Launch key initiatives that align with business objectives.

10. Strengthen Culture & Hiring Strategy

  • Set a strong engineering culture with best practices.
  • Define hiring needs and attract top talent.
  • Improve retention by fostering a collaborative, innovative environment.

11. Measure & Iterate

  • Establish key metrics (e.g. uptime, deployment frequency, lead time).
  • Monitor progress and adjust strategy based on results.
  • Provide regular updates to the CEO and stakeholders.

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